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My friends and I play a fair amount of Settlers of Catan (normally with 3-4 players). Sometimes I do well and sometimes I do badly; however, the most infuriating games are those where I'm unable to do anything for pretty much the entire game.

For example, in the last game with 4 players, I managed to (in total) build 3 roads and buy 2 development cards (a knight and a victory point). As the starting player, I placed my first settlement in a strong central position in the map with good access to both wood and brick. However, by the time everyone else placed their cities, I was forced to place my last city on the coast to get access to any ore, and I was left completely cut off from wheat (and my other settlement).

My problems became fairly evident in the early stages of the game - without access to wheat, I struggled to gather the resources to build new settlements, and to make matters worse, my initial settlement placement was very hemmed in by other players, meaning I didn't have many options on where to expand to. By the time I managed to scrape together the resources to build a settlement, other players had already built settlements too close, meaning I needed to use up my resources to build more roads. Trading with other players didn't really help me out, as they were all racing for the same settlement positions that I was.

These sorts of games seem to come around reasonably frequently, which leads me to believe that it's something that I'm doing rather than just being something that happens every now and then.

7 Answers
7

There are many ways to win at Settlers. The only type of starting position which limits your options is the one you described - good access to wood and brick but not much else, and then getting hemmed in. This situation doesn't happen too often in our group because the more experienced players usually dissuade newer or poorer players from placing an initial settlement that has a strong likelihood of leading to a disastrous outcome - which reduces the chance of a tedious game for all.

However, I've seen many poor starts in Settlers that ended in victory. I have two sections worth of thoughts for you describing the advantages of starting out behind, and the various ways I've seen players come back after a poor start.

The advantages of starting from behind:

other players more willing to trade with you

you can drive a harder bargain in trades (i.e. you must give me 2 cards to get the 1 you need, or you must give me 3 cards to get the 2 you need)

the robber gets put on you less often

when the robber does get put on you, the card is drawn from a different player's hand if hex is shared

people don't pay as much attention to what you're doing, so you can be secretly planning for your dramatic surge to victory without everyone pointing out what you're planning (good players tend to carefully monitor and point out who is close to winning and why but often neglect this analysis for those who trail by a lot)

Various ways to win with seemingly poor initial starting positions

monopolize a scarce resource and obtain advantaged trades (something the player going first is sometimes best positioned to do)

go for a 2:1 port strategy if circumstances allow

if placing first, consider carefully where the good settlement sites are for initial placement. You might purposely shift to a slightly worse settlement site because it is obvious nobody else will place near it (or maybe one side will obviously be open for expansion). You will often need to very carefully place the second settlement to preserve a swath of territory for yourself to pull off this strategy. I have often started slow because I purposely chose slightly worse resources for this reason, but had far more expansion territory than the other players who end up crowding each other while I slowly catch up and eventually surpass them.

Ultra-cooperate your way to a chance at victory. I had a game recently where I got off to an extremely unlucky start getting cut off from my two best expansion possibilities (which literally had only a 1/6 chance of happening). Another player also started poorly and we both still had 2 settlements while the other two players already each had 4-5 VPs worth of cities and settlements each. So we started doing hugely helpful trades to each other - so he would give me an ore for my whole hand on one turn so he could build his first settlement. Then I gave him a brick for his entire hand to build my first city . . . and so forth. We broke off cooperation when we were both in the lead and he won but you get the idea.

Get other players fighting against each other. Point out who is winning and why, and convince everyone to gang up on that person until someone else gets the lead then do the same thing to that person. That can give you a lot of time to catch up.

Most important: Make sure you have some way to access wheat and ore, even if it's just a way you can expand to get them or someone who you're pretty sure will be willing to trade with you (See Which of the 5 resources in Settlers of Catan (base version) is most important? Why?). You have many more options with these resources, whereas brick/wood strategies require either a port (preferably 2:1) or lots of expansion territory to work. I literally once won a game without any brick or wood, and without building a single road, when I was cut off early (see picture below: white, with 15 development cards)

"Another player [and I] started doing hugely helpful trades to each other." Reminds me of the story of two graduates of the naval academy who made a secret pact to talk each other up at every possibility. Both became Admirals.
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Tom AuOct 6 '12 at 18:15

I'll contribute one suggestion: I don't think that prioritizing placements that offer brick and wood is a very sensible philosophy. Yes, those resources maximize your chances of coming strong out of the gates with early roads. On the other hand, dominating in the early game is only a small part of being good at Settlers of Catan. You're discovering that you often end up powerless in the mid-to-late game. I'd say it's very likely that your focus on early-game resources is contributing to this problem.

Suppose you grab two plum locations for brick and/or wood - if they're on opposite sides of the map, with other players in the way, your ability to connect your roads together will be severely hampered, maybe to the extent of cancelling out the advantage you gained from cornering road-building resources in the first place. And here's another thing: by apparently doing quite well in the early game with your wood, brick and roads, you strongly incentivize other players to do something to contain your position. Meanwhile, the player who is unassumingly building up a nice collection of development cards is probably actually doing better than you. Subtlety is a great virtue in Catan!

If I were you, I'd try aiming for abundance of resources and two placements that are harmonious with one another, in strong preference to this notion of "I mustn't do badly in the early game". I think you may find it reaps dividends, and even if you crash and burn a few times at least it'll provide you with some interesting new perspectives in ways to try and win the game.

if they're on opposite sides of the map, with other players in the way, your ability to connect your roads together will be severely hampered -- who cares about connecting roads? I often go for wood and brick to claim territory (with settlements) before others claim it, the longest road is a trap for novices. I'm yet to see the situation where the collection of dev cards leads to the better position, because more settlements increases production, resource diversity, and number diversity, in an ongoing way. And victory points!
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Eric WilsonFeb 4 at 13:50

First, the most important big strategy tip for Catan: there is no single winning strategy. You must adapt to the board and to your current circumstances. There are many possible successful strategies (e.g., roads + settlements; cities; or single resource + port), but trying to run a particular strategy in inappropriate conditions can easily lead to stagnation.

By the same token, there is no single essential resource. Getting production of a variety of resources is certainly very helpful, but in my experience, it's not worth giving up very much total production to get that. In the particular example you gave, you had one settlement that had good road production but was blocked in. In order to take advantage of your ability to build roads, I would want to place the second settlement somewhere with decent production (probably all the good ones were taken, but the coast is usually even worse) and room for expansion.

However, in my experience, when players stagnate, it is most often not a result of poor initial placement, but of mistakes in the early- and mid-game play. Here are two specific tips:

Be focused but flexible in your building strategy. Decide what you need to do to grow and do what you need to do to make that happen. You said you bought two development cards. That was probably a mistake -- you were blocked in, so you needed to build cities. That means you need to save up ore and grain until you can do that. Don't be tempted to buy something that you don't need, because it means wasting resources and slowing your development. This is a very common way for novices to stagnate. However, if circumstances change or the dice turn up a bunch of resources useful for another strategy, don't be afraid to change your goal.

Trade, trade, trade. If you are missing a resource you need, you must trade for it. If that means trading 4-1 with the bank, or 2-1 or even 3-1 with another player, then do that. One resource card that lets you build something valuable is worth much more than 3 or 4 cards that don't. Also, keep your plan in mind when trading comes around. Suppose you don't have ore production but need to build cities -- then whenever someone is offering to trade ore, see if you can buy it. For the first ore, it may seem futile, since you need two more, but save them up and eventually you will be able to build your city. I should add that you should also consider trading for a resource you need even if you have good production of it but simply don't have any right now. Mostly you will only want to do this if you can build right away with it, but in that case it can certainly be worthwhile -- a new settlement now is worth substantially more than one in one or two turns.

Another factor that can sometimes cause stagnation is bad dice rolls. If your production is concentrated on two or three numbers, and those number don't come up much, you won't be able to do very much. This is not necessarily bad strategy, just high variance: sometimes you will gets lots of resources, sometimes very little. A single game is not long enough for the randomness to reliably even out.

First seat is usually one of the worst places to be in my opinion. It will guarantee you the best and the lest desirable placements on the board. Every seat has different placement strategies associated with them but I will try to be more general.

Resources alone is not the only thing to consider on initial placement. Rolling ratios and good rolling ratio combinations are also critical to success. I tend to look with intersections containing 10-8-5 or 9-6-4 intersections as well as if they produce the resources to build roads and eventually cities. Even if you have a high ratio placement with similar resources (i.e. 2 wheat and one sheep on a 10-9-6) getting the resources will usually overcome the lack of the proper variety of resources. You have to have something to trade in order to trade is the point.

Even if you can place a second settlement on a port that has the resource (i.e. wheat port on a wheat hex with an 8) do not be tempted by it. Those placements will start producing only one card early in the game and make you a target to easily stunt your growth. You may want to consider a lower number placement but produces more resources.

Whenever someone wants to make a trade, tell them you'll give them what they're looking for in exchange for any two cards. I know a guy who has come from behind with this strategy so many times it's ridiculous. Everyone thinks they're just handing you their trash, but if you get enough of it it can still work out.

+1 for pointing out something I meant to say in my own answer - but as I read through it I realized I did not make it at all obvious. So I clarified what I meant by "you can drive a harder bargain." I have sometimes received a fistfull of cards (like 3 for 1 or 5 for 2) when I'm very far behind because the person in the lead wanted to build their next city but nobody else would trade with them. Also, although this was mentioned in my answer and one other, it is so vital to coming back from behind that it's worth it's own separate answer.
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Joe GoltonOct 2 '12 at 14:36

Judging from the games I've played of Settlers, of the fraction which isn't luck based, about 75% of your win-chance is from initial settlement placement, with the remainder down to strategy. This is partly because your initial settlement placement dictates your strategy, and trying to change it afterwards will normally end badly.

When looking at the board, you need to be able to identify which resources will be in demand, and where all the starting settlements will be. You might not be able to accurately predict which players will go where, but you should be able to identify ~9 spots for a 4 player game of which 8 will have starting settlements placed on them. The only thing to watch out for it when one location will block 1-2 other likely starting places, which can severely restrict the choice of the last player.

Unless you are going for the very unlikely 2City, 4VPcard+largest army strategy, you will want to take 2 settlements. Since you get 2 free roads, you should place these in a direction to get a new settlement. It is very important NOT to place your free roads towards a location someone else will probably place a starting settlement, as then you have wasted your free road! Place them heading out to the coast is normally good, as there is plenty of room for settlements on the coast while there will normally be very minimal room in the interior. It doesn't even matter if you get decent resources from your 2 settlements, they are VPs and allow more cities to be built for even more VPs. If they get you a port or more resources, then that's a bonus.

In your game, you went first which is probably the worse position to be in. However, you should evaluate where everyone else will probably go before placing your settlement. If you think you won't get access to both wheat and ore, then don't place your first settlement where you did, going for the best ore location is rarely a bad move! Then when you come at the end to place your second settlement, you are in the unique position of getting to go immediately afterwards. This lets you do cunning tricks such as placing it on a wood/brick location (even if poor numbers) to start with those resources, then immediately building a road which combined with your free one can be used to block another player's starting road for a race to a good location.

Sometimes there simply isn't anything you can do about it. There are a whole load of good suggestions on here, but actually changing the game through extensions can help somewhat, changes that I've found reduce this problem:

5-6 player extension, gives you a bigger map so you block each other less and have a greater variety of hex's to choose from.

Seafarers - there are more paths for navigation so you don't get blocked in and can earn victory points/explore using different resources.

Cities & Knights - Change the tactics, people who are winning have to do things to slow themselves down (e.g. buying knights) which can help, and some upgrades allow you to collect cards even if you're numbers aren't coming up.

Distributed Dice - Using a deck of cards (or settlers dice cards if you've got traders & barbarians) allows the hex numbers to come up in a distributed way, reducing the chances of you never collecting your resources.